Nitrate ester derivatives from epoxides using CAN: Efficient preparation of key intermediates in the synthesis of 4-alkoxytrinems

Tetrahedron Letters

Volumn 38, Issue 20, 1997, Pages 3587-3590

  Di Fabio, Romano ^a   Rossi, Tino ^a   Thomas, Russell J ^a  

^a GSK   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; ANTIINFECTIVE AGENT; TRINEM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030958694     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00670-9     Document Type: Article

References (23)

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2. Di Modugno, E; Erbetti, I.; Ferrari. L; Galassi, G; Hammond, S.H.; Xerri, L. Antimicrob. Agents Chemother. 1994, 38, 10, 2362; Tamburini, B.; Perboni, A.; Rossi, T.; Donati, D.; Andreotti, D.; Gaviraghi, G.; Carlesso, R.; Bismara, C. Eur. Pat. Appl. 416,953 (C07D477/00), March 13, 1991; Tamburini, B; Perboni, A; Donati, D; Andreotti, D.; Biondi, S.; Bismara, C. Eur. Pat. Appl. 416,952 (C07F7/18) 1991.
3. Di Modugno, E; Erbetti, I.; Ferrari. L; Galassi, G; Hammond, S.H.; Xerri, L. Antimicrob. Agents Chemother. 1994, 38, 10, 2362; Tamburini, B.; Perboni, A.; Rossi, T.; Donati, D.; Andreotti, D.; Gaviraghi, G.; Carlesso, R.; Bismara, C. Eur. Pat. Appl. 416,953 (C07D477/00), March 13, 1991; Tamburini, B; Perboni, A; Donati, D; Andreotti, D.; Biondi, S.; Bismara, C. Eur. Pat. Appl. 416,952 (C07F7/18) 1991.
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5. Tamburini, B; Rossi, T.; Donati, D.; Tarzia, G.; Gaviraghi, G. Recent Advances in the Chemistry of the Antiinfective Agents 1992, Bentley, P.H.; Ponsford, R. Ed., p. 21. Ghiron, C.; Piga, E.; Rossi, T.; Tamburini, B.; Thomas, R. J. Tetrahedron Lett. 1996, 37, 3891. Andreotti, D.; Rossi, T.; Gaviraghi, G.; Donati, D.; Marchioro, C.; Di Modugno, E.; Perboni, A. Bioorg. Med. Chem. Lett. 1996, 4, 6, 491. Panunzio,M,; Camerini, R.; Pachera, R.; Donati, D.; Marchioro, C.; Perboni. A. Tetrahedron Asymmetry, 1996, 7, 10, 2929. Camerini, R.; Panunzio, M.; Bonanomi, G.; Donati, D.; Perboni, A. Tetrahedron Lett. 1996, 37, 14, 2467. For alternative synthetic route s for the preparation of intermediate 3 see: Rossi, T.; Biondi, S.; Contini, S.; Thomas, R.J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 37, 9604. Bismara, C.; Donati, D.; Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello P. J. Org. Chem, in press.
6. Tamburini, B; Rossi, T.; Donati, D.; Tarzia, G.; Gaviraghi, G. Recent Advances in the Chemistry of the Antiinfective Agents 1992, Bentley, P.H.; Ponsford, R. Ed., p. 21. Ghiron, C.; Piga, E.; Rossi, T.; Tamburini, B.; Thomas, R. J. Tetrahedron Lett. 1996, 37, 3891. Andreotti, D.; Rossi, T.; Gaviraghi, G.; Donati, D.; Marchioro, C.; Di Modugno, E.; Perboni, A. Bioorg. Med. Chem. Lett. 1996, 4, 6, 491. Panunzio,M,; Camerini, R.; Pachera, R.; Donati, D.; Marchioro, C.; Perboni. A. Tetrahedron Asymmetry, 1996, 7, 10, 2929. Camerini, R.; Panunzio, M.; Bonanomi, G.; Donati, D.; Perboni, A. Tetrahedron Lett. 1996, 37, 14, 2467. For alternative synthetic route s for the preparation of intermediate 3 see: Rossi, T.; Biondi, S.; Contini, S.; Thomas, R.J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 37, 9604. Bismara, C.; Donati, D.; Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello P. J. Org. Chem, in press.
7. Tamburini, B; Rossi, T.; Donati, D.; Tarzia, G.; Gaviraghi, G. Recent Advances in the Chemistry of the Antiinfective Agents 1992, Bentley, P.H.; Ponsford, R. Ed., p. 21. Ghiron, C.; Piga, E.; Rossi, T.; Tamburini, B.; Thomas, R. J. Tetrahedron Lett. 1996, 37, 3891. Andreotti, D.; Rossi, T.; Gaviraghi, G.; Donati, D.; Marchioro, C.; Di Modugno, E.; Perboni, A. Bioorg. Med. Chem. Lett. 1996, 4, 6, 491. Panunzio,M,; Camerini, R.; Pachera, R.; Donati, D.; Marchioro, C.; Perboni. A. Tetrahedron Asymmetry, 1996, 7, 10, 2929. Camerini, R.; Panunzio, M.; Bonanomi, G.; Donati, D.; Perboni, A. Tetrahedron Lett. 1996, 37, 14, 2467. For alternative synthetic route s for the preparation of intermediate 3 see: Rossi, T.; Biondi, S.; Contini, S.; Thomas, R.J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 37, 9604. Bismara, C.; Donati, D.; Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello P. J. Org. Chem, in press.
8. Tamburini, B; Rossi, T.; Donati, D.; Tarzia, G.; Gaviraghi, G. Recent Advances in the Chemistry of the Antiinfective Agents 1992, Bentley, P.H.; Ponsford, R. Ed., p. 21. Ghiron, C.; Piga, E.; Rossi, T.; Tamburini, B.; Thomas, R. J. Tetrahedron Lett. 1996, 37, 3891. Andreotti, D.; Rossi, T.; Gaviraghi, G.; Donati, D.; Marchioro, C.; Di Modugno, E.; Perboni, A. Bioorg. Med. Chem. Lett. 1996, 4, 6, 491. Panunzio,M,; Camerini, R.; Pachera, R.; Donati, D.; Marchioro, C.; Perboni. A. Tetrahedron Asymmetry, 1996, 7, 10, 2929. Camerini, R.; Panunzio, M.; Bonanomi, G.; Donati, D.; Perboni, A. Tetrahedron Lett. 1996, 37, 14, 2467. For alternative synthetic route s for the preparation of intermediate 3 see: Rossi, T.; Biondi, S.; Contini, S.; Thomas, R.J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 37, 9604. Bismara, C.; Donati, D.; Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello P. J. Org. Chem, in press.
9. Tamburini, B; Rossi, T.; Donati, D.; Tarzia, G.; Gaviraghi, G. Recent Advances in the Chemistry of the Antiinfective Agents 1992, Bentley, P.H.; Ponsford, R. Ed., p. 21. Ghiron, C.; Piga, E.; Rossi, T.; Tamburini, B.; Thomas, R. J. Tetrahedron Lett. 1996, 37, 3891. Andreotti, D.; Rossi, T.; Gaviraghi, G.; Donati, D.; Marchioro, C.; Di Modugno, E.; Perboni, A. Bioorg. Med. Chem. Lett. 1996, 4, 6, 491. Panunzio,M,; Camerini, R.; Pachera, R.; Donati, D.; Marchioro, C.; Perboni. A. Tetrahedron Asymmetry, 1996, 7, 10, 2929. Camerini, R.; Panunzio, M.; Bonanomi, G.; Donati, D.; Perboni, A. Tetrahedron Lett. 1996, 37, 14, 2467. For alternative synthetic route s for the preparation of intermediate 3 see: Rossi, T.; Biondi, S.; Contini, S.; Thomas, R.J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 37, 9604. Bismara, C.; Donati, D.; Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello P. J. Org. Chem, in press.
10. Tamburini, B; Rossi, T.; Donati, D.; Tarzia, G.; Gaviraghi, G. Recent Advances in the Chemistry of the Antiinfective Agents 1992, Bentley, P.H.; Ponsford, R. Ed., p. 21. Ghiron, C.; Piga, E.; Rossi, T.; Tamburini, B.; Thomas, R. J. Tetrahedron Lett. 1996, 37, 3891. Andreotti, D.; Rossi, T.; Gaviraghi, G.; Donati, D.; Marchioro, C.; Di Modugno, E.; Perboni, A. Bioorg. Med. Chem. Lett. 1996, 4, 6, 491. Panunzio,M,; Camerini, R.; Pachera, R.; Donati, D.; Marchioro, C.; Perboni. A. Tetrahedron Asymmetry, 1996, 7, 10, 2929. Camerini, R.; Panunzio, M.; Bonanomi, G.; Donati, D.; Perboni, A. Tetrahedron Lett. 1996, 37, 14, 2467. For alternative synthetic route s for the preparation of intermediate 3 see: Rossi, T.; Biondi, S.; Contini, S.; Thomas, R.J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 37, 9604. Bismara, C.; Donati, D.; Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello P. J. Org. Chem, in press.
11. Tamburini, B; Rossi, T.; Donati, D.; Tarzia, G.; Gaviraghi, G. Recent Advances in the Chemistry of the Antiinfective Agents 1992, Bentley, P.H.; Ponsford, R. Ed., p. 21. Ghiron, C.; Piga, E.; Rossi, T.; Tamburini, B.; Thomas, R. J. Tetrahedron Lett. 1996, 37, 3891. Andreotti, D.; Rossi, T.; Gaviraghi, G.; Donati, D.; Marchioro, C.; Di Modugno, E.; Perboni, A. Bioorg. Med. Chem. Lett. 1996, 4, 6, 491. Panunzio,M,; Camerini, R.; Pachera, R.; Donati, D.; Marchioro, C.; Perboni. A. Tetrahedron Asymmetry, 1996, 7, 10, 2929. Camerini, R.; Panunzio, M.; Bonanomi, G.; Donati, D.; Perboni, A. Tetrahedron Lett. 1996, 37, 14, 2467. For alternative synthetic route s for the preparation of intermediate 3 see: Rossi, T.; Biondi, S.; Contini, S.; Thomas, R.J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 37, 9604. Bismara, C.; Donati, D.; Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello P. J. Org. Chem, in press.
12. 4-Acetoxy-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone is commercially available from Kaneka America Corp., New York, N.Y. and from Aldrich Chemical Company Inc., Milwaukee, Wis.,
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18. Iranpoor, N.; Baltork, I. Mohammadpour Synth. Commun. 1990, 20, 18, 2789. After the completion of this work the following publication, dealing with the opening of epoxides with CAN alone or in the presence of an excess of nitrate, appeared: Iranpoor, N.; Salehi, P. Tetrahedron 1995, 51, 3, 909.
19. Iranpoor, N.; Baltork, I. Mohammadpour Synth. Commun. 1990, 20, 18, 2789. After the completion of this work the following publication, dealing with the opening of epoxides with CAN alone or in the presence of an excess of nitrate, appeared: Iranpoor, N.; Salehi, P. Tetrahedron 1995, 51, 3, 909.
20. Green, T.W., in Protective Groups in Organic Synthesis. 1981, John Wiley & Sons Ed., New York.
21. This reaction was proven to be general using different types of epoxides. In particular, when the reaction was attempted on cyclohexene oxide and styrene oxide the nitro derivatives 10 and 11 were obtained with complete regio and stereoselection, in reasonable yields after purification by flash cromatography.
22. Corey, E.J.; Hopkins, Paul B. Tetrahedron Lett. 1982, 23, 4871.
23. All new compounds were characterised by routine analytical and spectroscopic methods.